Stop Trying to Ask Good Questions

Many leadership practices and coaching competencies outline rules for asking good questions. Common ones include: Ask open questions that start with What, When, Where, and How. Avoid Why questions.

These suggestions are misleading.

It is more important that you are clear about your intent, the emotions you feel when you ask the questions, and your judgment about the person you are talking to.

Additionally, the time you spend trying to find a good question to ask, is time you are in your head and not present to the person you are with. As I say in The Discomfort Zone, “They want you to be present more than they need you to be perfect.”

What is the intention of your questions?

The person must feel your intentions are in their best interest throughout the conversation. As soon as you shift to wanting them to learn something or change because you think they should, they will feel pushed even if you are asking open questions.

Consider your intention when asking, “What did you think would happen? When did you decide they were wrong? Where is this likely to happen?” If you are asking out of curiosity and a desire for clarity, your questions will stimulate self-reflection. If your intention is to get them to see the faults in their thinking, they will see you trying to convince them they are wrong instead of working to find a solution. They will either become defensive or shut down instead of open up.

Even a Why question can be good if you are asking with compassionate curiosity.

You must have an emotional intention focused on helping the person achieve the result they want or on an outcome that you both want. Clearly state this intention up front – define the outcome you want to help the person achieve that they desire as well. People need to feel you genuinely care about their desires or they will assume you just want them to think like you.

What emotions are you feeling when you deliver your questions?

Even if you go into the conversation feeling calm and centered, you may feel impatient, uncomfortable, or eager to help while they are describing their situation. These emotions make your questions feel judgmental or pushy, as if you are criticizing them and/or leading them to what you want them to see. They will feel you are trying to convince them or quiet them. They will react with irritation, compliance, or retreat.

Notice when you begin to feel irritated and impatient. Catch your urge to interrupt or when you start explaining your questions. Exhale – let the tension subside.

Recall the positive intention you had for the conversation in the first place. Restate your intention before you ask what would be most important for them to look at next.

Do your best not to get tangled in their reactions. If you are calm, comfortable. and present to the other person, you are better able to use your questions to help them reflect and discover.

Do your questions reflect respect for the person regardless if you disagree?

An open conversation requires a feeling of mutual respect. Ensure you trust the person’s ability to grow or rebuild your respect if you need to before your enter the conversation. They will not hear you if you “know better” and talk as if they are ignorant. Even if you disagree with their perspective, honor the person anyway. Then ask if you can share your opinion or something you learned from past experience. Offering an opinion is easier to hear than presenting facts that make someone wrong or inadequate.

Reflections can lead to good questions

I believe that summarizing what someone is telling you – including encapsulating the major elements of their story in just a few words – and then asking a question that arises from your curiosity is better than worrying about forming a good question. Try to help them objectively observe their story so they may see beyond their limited perspective.

Even closed questions that follow your summaries such as, “Is this correct? Do you want to change this pattern? Is this what bothers you most?” can be powerful clarifiers. Yes, it would be good to know, “What would you like to have instead of this situation? When did this first become a problem for you? What’s stopping you from deciding or taking action?” but don’t spend time trying to remember these questions if they don’t emerge from your curiosity.

Instead of trying to remember or frame your questions correctly, exhale, softy see the person with compassion and care, and then trust they can find a way forward if you stay keenly interested in their perspective and choices. Your questions will be good.